Cyclobutylamine → HCID 131724928, compound

HRID 1353934Notes

Reaction equation

HRID 1353934 reaction equation
C([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)[N:7]=[C:6]2[C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=O)#N.[CH:27]1([NH2:31])[CH2:30][CH2:29][CH2:28]1.C1C=CC2N(O)N=[N:38][C:36]=2C=1.CCN=C=NCCCN(C)C.Cl>C1COCC1.CN(C=O)C>[C:36]([CH:15]1[CH2:14][O:13][CH:12]([N:8]2[C:9]3[C:5](=[CH:4][CH:3]=[CH:11][CH:10]=3)[C:6]([C:18]3[CH:19]=[C:20]([C:21]([NH:31][CH:27]4[CH2:30][CH2:29][CH2:28]4)=[O:23])[CH:24]=[CH:25][CH:26]=3)=[N:7]2)[CH2:17][CH2:16]1)#[N:38]

Participants

7

Reactant 4

HCID 75645CyclobutylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22480305HCID 22480305, compound

Product 1

HCID 131724928HCID 131724928, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared in a similar fashion to that of Example 367 A using the following amounts of reagents: 3-(5-cyano-1-perhydro-2H-pyran-2-yl-1H-indazol-3-yl)benzoic acid (800 mg, 2.29 mmol), cyclobutyl amine (738 μL, 8.64 mmol), HOBT (1.17 g, 8.70 mmol), EDAC.HCl (1.67 g, 8.70 mmol) in anhydrous THF (25.0 mL) and anhydrous DMF (7.0 mL). Precipitation from methanol and ethyl acetate with hexanes afforded the desired compound (826 mg, 72% yield) as an off-white powder. ES-MS (m/z) 401 [M+H]+.

Workup

  1. customThe title compound was prepared in a similar fashion to that of Example 367 A using the following amounts of reagents
  2. customPrecipitation from methanol and ethyl acetate with hexanes

Sources & evidence

ORD record
ord-8caf917a53ca431bb01718f3aed5e714
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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